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Triethylamine → 8-(2-Methyl-6-methoxycarbonylaminobenzylamino)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine

HRID 2073800
Notes
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Reaction equation

HRID 2073800 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH2:12][C:13]#[CH:14])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:32]([O:34][CH3:35])=[O:33])[C:24]=1[CH2:25]Cl>CO>[CH3:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:32]([O:34][CH3:35])=[O:33])[C:24]=1[CH2:25][NH:1][C:2]1[C:3]2[N:4]([C:8]([CH2:12][C:13]#[CH:14])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143684802-Methyl-6-methoxycarbonylaminobenzyl chlorideHCID 144998058-Amino-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 144998258-(2-Methyl-6-methoxycarbonylaminobenzylamino)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridineYield 38.8%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

To a solution of 8-amino-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (8.0 g) and triethylamine (4.8 g) in methanol (80 ml) was added 2-methyl-6-methoxycarbonylaminobenzyl chloride (10.15 g) and the mixture was stirred at room temperature for 17 hours. After methanol was evaporated in vacuo, the resultant residue was dissolved in methylene chloride (100 ml) and the mixture was washed with water and dried over magnesium sulfate. The solvent was evaporated in vacuo. The resultant residue was subjected to column chromatography on silica gel (240 g) and eluted with a mixture of chloroform and ethyl acetate (20:1) to give a crystalline product. The crystals were recrystallized from a mixture of ethyl acetate and n-hexane to give 8-(2-methyl-6-methoxycarbonylaminobenzylamino)-3-(2-propynyl)-2-methylimidazo[1,2-a]pyridine (6.08 g).

Workup

  1. customAfter methanol was evaporated in vacuo
  2. dissolutionthe resultant residue was dissolved in methylene chloride (100 ml)
  3. washthe mixture was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. washeluted with a mixture of chloroform and ethyl acetate (20:1)
  7. customto give a crystalline product
  8. customThe crystals were recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-667a7a3e21ed4e049018afdfeeeac1ca
Source dataset
uspto-grants-1990_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04920129

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes